Hickey and Squaw Loop

MODERATE 172 reviews

Hickey and Squaw Loop is a 2.8 mile lightly trafficked loop trail located near Stockbridge, Massachusetts that features beautiful wild flowers and is rated as moderate. The trail offers a number of activity options and is accessible year-round. Dogs are also able to use this trail but must be kept on leash.

2.8 miles
685 feet

dogs on leash

kid friendly


cross country skiing


nature trips


trail running


bird watching



wild flowers




1 month ago

perfect, quick winter day hike.
a little icy at top along red trail

3 months ago

Great views in all directions, not too hard, fun to climb over rocks near the top.

3 months ago

Very satisfying hike, though a bit crowded. Beautiful views at top.

4 months ago

Fall trails conditions as in any NE area. Mixed wet day yesterday in area, planned a weather break day amidst the Berkshires & had one. As a first time, chose the Blue Indian Monument Inscription Trail. An old wagon trail ending proximate to the Red Summit Squaw Trail. An easy south shoulder to summit climb, gradual ascent. The Red & Yellow Hickey Trails meet at the Monument. The red then used scrape & ledge & rocks (some as steps) to Squaw Mountain, clearly blazed. Children & newbies should be watched - the cliffs are real, a 900 foot drop. My altimeter read 1615-1640 height. A couple of “Pulpit” rock formations adjoin the cliff face here, one the Devil’s Pulpit. The trustees allow no rock climbing here. Descent can be had by the Squaw Trail Red .5 mile which intersects the 1.6 mile Blue Monument trail up or down. The .8 mile Hickey Yellow Trail is correctly styled strenuous. In fall, leaves conceal rocks & pits. Yellow blazes are adequate. Taken downhill the trail is 2/3 sharp incline & rocky. Very attentive. Two bridges & views of the lower cliff rockfalls & some flatter slopes appeal. All (the Red via the blue north or south, the Yellow at the Monument) commence & end at the picnic & parking area. If time, a ride back via State 183 to the West show a rich valley romantic view of the massif along the Housatonic River. The northern water from Squaw Mountain is Agawam Brook Pond. The trail condition is good. Weather turns a risk at the summit. Pay to park or donation encouraged with solar powered ATM/Debit/Credit machines.

4 months ago

Great for beginners

4 months ago

Always a great hike, in any season except in deep snow. Fab views from the top. Approx 1.5 hours to complete the loop. Dog friendly. Can be crowded on the weekends. Devil’s Pulpit is a short diversion near the top which affords less crowded views.

4 months ago

great hike with breathtaking views, I would definetely recommend squaw trail( red one) Not for kids under 10

5 months ago

Was looking for something in this area to do a easy or moderate loop. Found this and didn't realize I had actually gone past it when doing another hike out at Alander Mtn. a while back. This is a busy area, a hike that is more for somebody looking for something to do on a weekend than say a hiker looking to do a section of the AT. Don't get me wrong, it's nice but don't look for solitude. After seeing many people starting their loop by going right, I went left to start and did clockwise. Only saw a few people till I got towards the top. Still, some people are just loud and can't just enjoy the mountain. Glad I found some areas to explore before reaching the congested top area. There is a section just off the Squaw trail that is called Devil's Pulpit. It's just a little side trail so take it if you can. It brings you to the cliff area, straight down if you slip but no worries. :) All in all, a decent hike but nothing too exciting till you get to the Squaw trail. There is the Indian loop trail which goes alongside the mountain under the Squaw, probably worth checking out but wasn't that interested to back track and find out. Last thing to note as I didn't notice when I pulled into the parking lot but I guess you need or will have to pay to park. I walked by a kiosk getting back to my car. I checked it out, doesn't look like it had been activated yet but just letting you know for future reference. When I parked and started up the trail, I didn't go by this and there isn't a sign anywhere that mentions paying at least not yet.

6 months ago

Excellent! Easy parking, well marked trail with wonderful views. Highly recommend!

6 months ago

Nice views, easy to follow. put on your mountain goat for Boulder climbing!

7 months ago

Nice short hike with great views.

11 months ago

This hike is very popular, and for good reason. The Hickey Trail leads to the summit at a moderately steep grade. The Squaw Peak Trail then traverses the ridge, where there are great views of the Berkshires. Descend via the Indian Monument Trail, which is longer and more gradual than the Hickey Trail. My only criticisms are that despite its popularity, there are no restrooms at the bottom, and there are some large cliffs at the top.

11 months ago

I did this hike with my ten year old son. He is starting to enjoy hiking and so this was a perfect one for him. We took the Hickey trail which was a bit steep, made a few stops for him to catch his breath. Along this path, you will come to a nice small waterfall and stream. Right before hitting the summit, there was a cool little ledge with a nice view. Once you reach the peak, there is a 360 view. My son loved it. We then followed the Squawk peak train, into the Indian Monument trail back. This trail was pretty flat, that followed the along the main road. The entire hike took two hours, maybe slightly more. Nice... would recommend.

11 months ago

Always a nice hike although today it was quite muddy. But who can complain about a 70 degree day in February. A little ice but it and the mud was fairly easy to get around.

Friday, January 19, 2018

Fantastic Hike! Gold trail - great challenge. Beautiful views.

trail running
Monday, December 25, 2017

A good loop and challenging although the trails were very icy so I wasn’t able to make it all the way around and had to turn back. Look forward to going again in the spring.

Thursday, November 30, 2017

The steep, short side is the best! Definitely a beautiful Berkshire favorite!

Monday, November 27, 2017

went at 9am, only a few other people, quick hike. Gradual incline. Indian trail runs by the road, which is a luttle distracting, but the peak is great! Definitely recommend stopping at Devil's Pulpit for the best views.

Friday, November 03, 2017

Nice but traffic noise.

Thursday, November 02, 2017

Beautiful mountains with captivating views. Though it gets steep at certain points, the trek to Devil’s Pulpit is well worth the adventure!

Tuesday, October 24, 2017

Hiked this today on a warm fall day! Great foliage

Friday, October 06, 2017

Gorgeous views and a very easy ascent on the Indian Monument Trail to the left after you park. Ran into a few people but they were all very nice. Even met a hiking couple from Colorado. Good news, Atlas (German shepherd) did not go after any chipmunks! ;) Though there were tons! I posted photos. It gets a little tight at the top and Atlas didn't want to go over the rocks, but then we saw that there was a pass around. All in all 5 stars! Would go again in a heartbeat. Oh. Bring your debit card. There's a meter for paying for parking at the lot.

Saturday, September 23, 2017

Not super difficult, but I broke a pretty good sweat on the way up on an unseasonably-warm Fall day. The trail follows the road for a bit, so there's a good bit of noise, but eventually it meanders through the woods, climbing steadily until opening up to some pretty great views at the top. The trail was a bit rocky, interspersed with tree roots, but that's to be expected in this area.

Thursday, September 21, 2017

Beautiful views at the top with well marked trails. One of my favorite hikes!

Friday, September 15, 2017

We two 70+year-olds really enjoyed this trail. The difficulty was in the rocky terrain and not the elevation, so it was fun but not taxing.
The trailhead is NOT at Fountain Pond Park, as stated in this app. It has its own parking area at 551 Stockbridge Rd. in Great Barrington.

Saturday, September 09, 2017

Spectacular views from the exposed granite on the top in 360 degrees. Mostly anyone can do this hike. Good in all seasons.

Thursday, August 31, 2017

There are three principal trails at this site which can make a loop or can be done as in and out trails. HIckey trail is steeper and takes you to Summit Trail which goes to the summit with lovely views and takes you down by a gentler grade trail. Moderate level, and the trail is in good condition. The summit is a bit rocky and "ledge-y" in spots.

Wednesday, August 23, 2017

Easy hike, great view! Very well marked trails and very easy to find.

Saturday, August 19, 2017

Good hike with a nice view at the top.

Monday, August 14, 2017

Good times!

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